EP0098632A1 - Salts of acid ether sulphates and process for the preparation of these salts - Google Patents
Salts of acid ether sulphates and process for the preparation of these salts Download PDFInfo
- Publication number
- EP0098632A1 EP0098632A1 EP83200853A EP83200853A EP0098632A1 EP 0098632 A1 EP0098632 A1 EP 0098632A1 EP 83200853 A EP83200853 A EP 83200853A EP 83200853 A EP83200853 A EP 83200853A EP 0098632 A1 EP0098632 A1 EP 0098632A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- salts
- acid
- tri
- isopropanolamine
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 29
- 239000002253 acid Substances 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 3
- -1 ether sulphates Chemical class 0.000 title description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 14
- 229910021653 sulphate ion Inorganic materials 0.000 claims abstract description 14
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 8
- 238000006386 neutralization reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000350481 Pterogyne nitens Species 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- PZOIEPPCQPZUAP-UHFFFAOYSA-N 1-aminohexan-2-ol Chemical compound CCCCC(O)CN PZOIEPPCQPZUAP-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
- Y10S516/05—Organic amine, amide, or n-base containing
Definitions
- the invention relates to salts of acid ether sulphates that are liquid under normale temperature and pressure conditions as well as to the preparation of these salts.
- salts which have a very good surface activity, can be prepared by neutralization of acid sulphates of the general formula R(OCH 2 CH 2 ) n OS0 2 0H, where n represents a number having an average value of 2-3 and R an alkyl group with 8-16 carbon atoms with monobutylethanolamine, isopropylamine or di-ethylamine (see British patent specification 891.631).
- acid sulphates of the general formula R(OCH 2 CH 2 ) n OS0 2 0H, where n represents a number having an average value of 2-3 and R an alkyl group with 8-16 carbon atoms with monobutylethanolamine, isopropylamine or di-ethylamine (see British patent specification 891.631).
- sodium salts these known salts have the advantage that they do not have a pasty consistency under normal temperature and pressure conditions but are liquid, which not only cuts down transport cost but also is important for water-free applications of said salts.
- a disadvantage of these known salts
- the salts according to the invention are salts of acid sulphates of the general formula R(OCH 2 CH 2 ) n OS0 2 0H where n represents a number having an average value of 1-6 and R an oleyl group or an alkyl group with 8-16 carbon atoms with tri-isopropanolamine.
- n represents a number having an average value of 1.5-3.5, for instance the salt in which R represents a lauryl group and n an average value of 2.
- the acid sulphates of the said general formula can be obtained in a known way by condensing the corresponding alcohol ROH with epoxyethane in an amount corresponding with the desired average number of ethoxy groups and sulphating the reaction product formed. If a mixture of alcohols, for instance technical grade lauryl alcohol, is started from, the corresponding mixture of acid sulphates is obtained that can be converted to the corresponding mixture of salts according to the invention using tri-isopropanolamine. From the reaction product obtained by sulphation of the product formed upon condensation of the alcohol or the mixture of alcohols with epoxyethane, the di- and/or tri- ethoxy compound, for instance, may be isolated so that it can be applied for neutralization with tri-isopropanolamine.
- the neutralization of the acid sulphate with tri-isopropanolamine may for instance be effected by gradually adding the melted amine (melting point 58 °C) to the acid sulphate whilst stirring.
- the neutralization can be effected using reflux cooling or under pressure in a closed system.
- the temperature then is preferably chosen to be 35-45 °C, because this makes stirring of the reaction mixture easier than at normal ambient temperatures.
- For neutralization of a certain amount of acid sulphate such an amount of tri-isopropanolamine is needed as to give an aqueous solution of the end product obtained a pH of about 5.5.
- the salts according to the invention can be applied to various purposes, for instance as hair washing agent or as emulsifier in anhydrous systems such as anhydrous insecticide preparations.
- the invention will be elucidated in the following examples.
- the salts obtained according to these examples are practically odourless and have a light-yellow to yellow colour.
- the acid sulphate is neutralized with 211.5 g tipa.
- An amount of 616 g salt is obtained, the Epton value of which is calculated to be 1.43 mgeq/g.
- the salt After dilution with water to a concentration of 10 wt.-%, the salt has a pH of 5.2.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Salts of acid sulphates of the general formula R(OCH2CH2)nOSO2OH, where n represents a number having an average value of 1-6 and R an oleyl group or an alkyl group with 8-16 carbon atoms, with tri-isopropanolamine and process for the preparation of said salts wherein the acid sulphate in question is neutralized with tri-isopropanolamine.
Description
- The invention relates to salts of acid ether sulphates that are liquid under normale temperature and pressure conditions as well as to the preparation of these salts.
- It is known that such salts, which have a very good surface activity, can be prepared by neutralization of acid sulphates of the general formula R(OCH2CH2)nOS020H, where n represents a number having an average value of 2-3 and R an alkyl group with 8-16 carbon atoms with monobutylethanolamine, isopropylamine or di-ethylamine (see British patent specification 891.631). Compared with the corresponding, also known, sodium salts, these known salts have the advantage that they do not have a pasty consistency under normal temperature and pressure conditions but are liquid, which not only cuts down transport cost but also is important for water-free applications of said salts. A disadvantage of these known salts is, however, that their odour and colour are not ideal, rendering these salts less suitable for various applications. In addition it is difficult to dilute them with water because gel formation takes place.
- It has now been found that neutralization of various acid ether sulphates with tri-isopropanolamine may yield salts that not only have a suitable odour and colour but also are liquid under normal temperature and pressure conditions and furthermore can properly be dissolved in water without gel formation occurring.
- The salts according to the invention are salts of acid sulphates of the general formula R(OCH2CH2)nOS020H where n represents a number having an average value of 1-6 and R an oleyl group or an alkyl group with 8-16 carbon atoms with tri-isopropanolamine.
- Particularly suitable are the salts according to the invention where n represents a number having an average value of 1.5-3.5, for instance the salt in which R represents a lauryl group and n an average value of 2.
- The acid sulphates of the said general formula can be obtained in a known way by condensing the corresponding alcohol ROH with epoxyethane in an amount corresponding with the desired average number of ethoxy groups and sulphating the reaction product formed. If a mixture of alcohols, for instance technical grade lauryl alcohol, is started from, the corresponding mixture of acid sulphates is obtained that can be converted to the corresponding mixture of salts according to the invention using tri-isopropanolamine. From the reaction product obtained by sulphation of the product formed upon condensation of the alcohol or the mixture of alcohols with epoxyethane, the di- and/or tri- ethoxy compound, for instance, may be isolated so that it can be applied for neutralization with tri-isopropanolamine.
- The neutralization of the acid sulphate with tri-isopropanolamine may for instance be effected by gradually adding the melted amine (melting point 58 °C) to the acid sulphate whilst stirring. The neutralization can be effected using reflux cooling or under pressure in a closed system. The temperature then is preferably chosen to be 35-45 °C, because this makes stirring of the reaction mixture easier than at normal ambient temperatures. For neutralization of a certain amount of acid sulphate, such an amount of tri-isopropanolamine is needed as to give an aqueous solution of the end product obtained a pH of about 5.5. As the tri-isopropanolamine is not a strong base and the acid sulphate has a strongly acid character, and because of the presence of acid impurities, this neutralization requires an amount of amine that is larger than the stoichiometric amount.
- The salts according to the invention can be applied to various purposes, for instance as hair washing agent or as emulsifier in anhydrous systems such as anhydrous insecticide preparations.
- The invention will be elucidated in the following examples. The salts obtained according to these examples are practically odourless and have a light-yellow to yellow colour.
- Technical-grade octyl alcohol is condensed with 3.3 moles epoxyethane per mole alcohol. While being stirred, the product obtained (345 g) is sulphated with 150 g HS03Cl, which is gradually added in 30 minutes' time. The temperature increases to about 33 °C. The reaction mixture obtained is subsequently kept at 40 °C for 40 minutes while being stirred. An amount of 451 g acid sulphate is obtained, the Epton value of which is calculated to be 2.77 milligramme equivalents per g.
- Of the acid sulphate obtained, 448.5 g is neutralized with 267 g tri-isopropanolamine (hereinafter referred to as tipa) at 40 °C. Thus, 713 g salt with an Epton value of 1.58 mgeq/g is obtained. After addition of 4 g acetic acid and dilution with water of the product obtained to a concentration of 10 wt.-%, the pH of the aqueous solution is 5.1.
- In 30 minutes 120 g HS03Cl is gradually added to 348 g of a condensation product that is commercially available under the name Syn- peronic (3 moles epoxyethane per mole of a mixture of C11-C13 alcohols, available under the name synprol), which is meanwhile being stirred. The temperature increases to 35 °C.
- While being stirred, and while nitrogen is passed through it, the resulting mixture is subsequently kept at 38 °C for 40 minutes. An amount of 433.5 g acid sulphate is obtained, with a calculated Epton value of 2.31 mgeq/g.
- At a temperature of 40 °C, 404.5 g of the acid sulphate is neutralized with 211.5 g tipa. An amount of 616 g salt is obtained, the Epton value of which is calculated to be 1.43 mgeq/g. After dilution with water to a concentration of 10 wt.-%, the salt has a pH of 5.2.
- In 3.5 hours' time 1489 g HS03Cl is gradually added to 2565 g of the product of condensation of technical-grade lauryl alcohol with 2 moles epoxyethane per mole alcohol, which is meanwhile being stirred. The temperature increases to about 35 °C. While being stirred, and while nitrogen is passed through it, the mixture obtained is subsequently kept at 40 °C for 45 minutes. An amount of 3329 g acid sulphate is obtained, the Epton value of which is calculated to be 2.7 mgeq/g.
- Of the acid sulphate obtained, 3275 g is neutralized with 1885 g tipa at about 40 °C. The yield is 5160 g, with an Epton value of 1.61 mgeq/g. The pH of the water-diluted salt (10 wt.-%) is 5.55.
- In 35 minutes' time 118 g HSO3Cl is gradually added to 392 g of the product of condensation of technical-grade oleyl alcohol with 3.2 moles epoxyethane per mole alcohol, which is meanwhile being stirred. The temperature increases to about 35 °C. While being stirred, and while nitrogen is passed through it, the mixture obtained is subsequently kept at 40 °C for 30 minutes. An amount of 486 g acid sulphate is obtained, the Epton value of which is calculated to be 2.02 mgeq/g.
- Of the acid sulphate obtained, 406 g is neutralized with 207 g tipa at 35-40 °C. An amount of 613 g salt is obtained, the Epton value being 1.25 mgeq/g. The pH of the water-diluted salt (10 wt.-X) is 5.2.
Claims (4)
1. Salts of acid sulphates of the general formula R(OCH2CH2)nOSO2OH, where n represents a number having an average value of 1-6 and R an oleyl group or an alkyl group with 8-16 carbon atoms, with tri-isopropanolamine.
2. Salts according to claim 1, where n represents a number with an average value of 1.5-3.5.
3. Salts according to claim 2, where R represents a lauryl group and n an average value of 2.
4. Process for the preparation of salts according to any one of claims 1-3, characterized in that the acid sulphate in question is neutralized with tri-isopropanolamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT83200853T ATE21892T1 (en) | 1982-06-12 | 1983-06-10 | SALTS OF ACID AETHERSULFATES AND PROCESS FOR THE PREPARATION OF THESE SALTS. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8202398 | 1982-06-12 | ||
| NL8202398A NL8202398A (en) | 1982-06-12 | 1982-06-12 | SALTS OF ACID ETHER SULPHATES AND METHOD FOR PREPARING THESE SALTS. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0098632A1 true EP0098632A1 (en) | 1984-01-18 |
| EP0098632B1 EP0098632B1 (en) | 1986-09-03 |
Family
ID=19839877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP83200853A Expired EP0098632B1 (en) | 1982-06-12 | 1983-06-10 | Salts of acid ether sulphates and process for the preparation of these salts |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4645627A (en) |
| EP (1) | EP0098632B1 (en) |
| AT (1) | ATE21892T1 (en) |
| DE (1) | DE3365853D1 (en) |
| NL (1) | NL8202398A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0337406A1 (en) * | 1988-04-12 | 1989-10-18 | HENKEL CORPORATION (a Delaware corp.) | Neutralized alkyl ether sulfuric acid half-ester compositions containing polyhydroxy oligomers |
| EP1869978A1 (en) * | 2006-06-21 | 2007-12-26 | Bayer CropScience AG | Low-foaming preparations for crop protection |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4218075A1 (en) * | 1992-06-01 | 1993-12-02 | Henkel Kgaa | Process for the preparation of low-odor fatty alcohol ether sulfate salts |
| US5770756A (en) * | 1993-02-04 | 1998-06-23 | The Procter & Gamble Company | Highly concentrated alkyl sulphate solutions |
| US6479546B1 (en) | 2000-07-26 | 2002-11-12 | The Regents Of The University Of California | Allosteric inhibitors of lipoxygenase |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB891631A (en) * | 1957-02-02 | 1962-03-14 | Chemische Fabriek Andrelon Nv | Liquid, surface-active amine salts of organic acid sulphates and their preparation |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2126054A (en) * | 1934-05-11 | 1938-08-09 | Standard Oil Dev Co | Emulsifying agent and method of preparing same |
| US2052027A (en) * | 1935-07-25 | 1936-08-25 | Benjamin R Harris | Branched chain octyl sulphate |
| US2303348A (en) * | 1937-12-06 | 1942-12-01 | Freeman | Method for modifying organic bodies to raise the transition temperature therein from nonfluid to fluid phase and the composition |
| US2686201A (en) * | 1952-01-23 | 1954-08-10 | Atlantic Refining Co | Alkyl-alkanol amine salts of alkylated aryl sulfonic acids |
| JPS5849600B2 (en) * | 1978-03-06 | 1983-11-05 | 花王株式会社 | Liquid shampoo - composition |
-
1982
- 1982-06-12 NL NL8202398A patent/NL8202398A/en not_active Application Discontinuation
-
1983
- 1983-06-10 EP EP83200853A patent/EP0098632B1/en not_active Expired
- 1983-06-10 DE DE8383200853T patent/DE3365853D1/en not_active Expired
- 1983-06-10 AT AT83200853T patent/ATE21892T1/en active
-
1985
- 1985-03-19 US US06/713,649 patent/US4645627A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB891631A (en) * | 1957-02-02 | 1962-03-14 | Chemische Fabriek Andrelon Nv | Liquid, surface-active amine salts of organic acid sulphates and their preparation |
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS, vol. 96, no. 2, 11th January 1982, page 114, no. 8526d, Columbus, Ohio, USA & SU - A - 859 356 (YASNAYA POLYANA EXPERIMENTAL COMBINE OF CARDBOARD AND PAPER CONTAINERS) 31-08-1981 * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0337406A1 (en) * | 1988-04-12 | 1989-10-18 | HENKEL CORPORATION (a Delaware corp.) | Neutralized alkyl ether sulfuric acid half-ester compositions containing polyhydroxy oligomers |
| EP1869978A1 (en) * | 2006-06-21 | 2007-12-26 | Bayer CropScience AG | Low-foaming preparations for crop protection |
| WO2007147500A1 (en) * | 2006-06-21 | 2007-12-27 | Bayer Cropscience Ag | Low-foaming preparations for crop protection |
| JP2009541233A (en) * | 2006-06-21 | 2009-11-26 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | Low-foam preparations for crop protection |
| EP2366287A3 (en) * | 2006-06-21 | 2012-05-16 | Bayer CropScience AG | Foam preparations for protecting plants |
| AU2007263337B2 (en) * | 2006-06-21 | 2013-10-24 | Bayer Cropscience Aktiengesellschaft | Low-foaming preparations for crop protection |
| CN101472473B (en) * | 2006-06-21 | 2013-11-13 | 拜尔作物科学股份公司 | Low-foaming formulations for plant protection |
| US8637432B2 (en) | 2006-06-21 | 2014-01-28 | Bayer Cropscience Ag | Low-foam preparations for crop protection |
| TWI484909B (en) * | 2006-06-21 | 2015-05-21 | Bayer Ip Gmbh | Low-foam preparations for crop protection |
| EA022098B1 (en) * | 2006-06-21 | 2015-11-30 | Байер Интеллектуэль Проперти Гмбх | Preparation for low-foaming and enhancement activity of water-soluble or partially water-soluble biologically-active substances, herbicidal composition, process for preparation thereof and controlling unwanted plant growth |
| US9215868B2 (en) | 2006-06-21 | 2015-12-22 | Bayer Intellectual Property Gmbh | Low-foam preparations for crop protection |
| EA022098B9 (en) * | 2006-06-21 | 2016-05-31 | Байер Интеллектуэль Проперти Гмбх | Preparation for low-foaming and enhancement activity of water-soluble or partially water-soluble biologically-active substances, herbicidal composition, process for preparation thereof and controlling unwanted plant growth |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0098632B1 (en) | 1986-09-03 |
| ATE21892T1 (en) | 1986-09-15 |
| US4645627A (en) | 1987-02-24 |
| NL8202398A (en) | 1984-01-02 |
| DE3365853D1 (en) | 1986-10-09 |
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